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Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration

Remir Grigorevich Kostyanovsky 1
Remir Grigorevich Kostyanovsky
, 
Pavel Evgenievich Dormov 1
Pavel Evgenievich Dormov
, 
Peteris T Trapencieris 2
Peteris T Trapencieris
, 
Boriss Strumfs 2
Boriss Strumfs
, 
Gulnara Konstantinovna Kadorkina 1
Gulnara Konstantinovna Kadorkina
, 
Ivan Ivanovich Chervin 1
Ivan Ivanovich Chervin
, 
Ivars Ya Kalvin's 2
Ivars Ya Kalvin's
10.1070/MC1999v009n01ABEH001047
Published 1999-02-16
Communication , Volume 9, Issue 1, 26-27
11
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Kostyanovsky R. G. et al. Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration // Mendeleev Communications. 1999. Vol. 9. No. 1. pp. 26-27.
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Kostyanovsky R. G., Dormov P. E., Trapencieris P. T., Strumfs B., Kadorkina G. K., Chervin I. I., Kalvin's I. Ya. Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration // Mendeleev Communications. 1999. Vol. 9. No. 1. pp. 26-27.
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TY - JOUR
DO - 10.1070/MC1999v009n01ABEH001047
UR - https://mendcomm.colab.ws/publications/10.1070/MC1999v009n01ABEH001047
TI - Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration
T2 - Mendeleev Communications
AU - Kostyanovsky, Remir Grigorevich
AU - Dormov, Pavel Evgenievich
AU - Trapencieris, Peteris T
AU - Strumfs, Boriss
AU - Kadorkina, Gulnara Konstantinovna
AU - Chervin, Ivan Ivanovich
AU - Kalvin's, Ivars Ya
PY - 1999
DA - 1999/02/16
PB - Mendeleev Communications
SP - 26-27
IS - 1
VL - 9
ER -
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@article{1999_Kostyanovsky,
author = {Remir Grigorevich Kostyanovsky and Pavel Evgenievich Dormov and Peteris T Trapencieris and Boriss Strumfs and Gulnara Konstantinovna Kadorkina and Ivan Ivanovich Chervin and Ivars Ya Kalvin's},
title = {Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration},
journal = {Mendeleev Communications},
year = {1999},
volume = {9},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1999v009n01ABEH001047},
number = {1},
pages = {26--27},
doi = {10.1070/MC1999v009n01ABEH001047}
}
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Kostyanovsky, Remir Grigorevich, et al. “Optically active 2,2-dimethyl-1,3,4-triazabicyclo[4.1.0]heptan-5-one: synthesis, spontaneous resolution and absolute configuration.” Mendeleev Communications, vol. 9, no. 1, Feb. 1999, pp. 26-27. https://mendcomm.colab.ws/publications/10.1070/MC1999v009n01ABEH001047.

Abstract

Bicycle (±)-1 crystallises as a conglomerate (space group P21) and undergoes spontaneous resolution on crystallisation from chloroform or acetone (16–44% ee). The absolute configuration (S)-(−)-1 was determined by synthesis from (S)-Ser-OMe; mutarotation due to the partial conversion of 1 into the corresponding isopropylidene 4 was observed in MeOH solution.

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